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Chester

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Chester Flights as Low as $88

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Fri, May 9 - Thu, May 15
MCO
Orlando Intl.
BDL
Bradley Intl.
$88 Roundtrip, found 1 hour ago
$88
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, May 9 from Orlando Intl. to Bradley Intl., returning Thu, May 15, priced at $88 found 1 hour ago
Breeze Airways
Fri, Jan 31 - Mon, Feb 3
MCO
Orlando Intl.
BDL
Bradley Intl.
$90 Roundtrip, found 2 days ago
$90
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 31 from Orlando Intl. to Bradley Intl., returning Mon, Feb 3, priced at $90 found 2 days ago
Frontier Airlines
Wed, Feb 26 - Sat, Mar 8
MCO
Orlando Intl.
BDL
Bradley Intl.
$115 Roundtrip, found 4 days ago
$115
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Feb 26 from Orlando Intl. to Bradley Intl., returning Sat, Mar 8, priced at $115 found 4 days ago
Breeze Airways
Thu, Jan 30 - Sun, Feb 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$119 Roundtrip, found 4 days ago
$119
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jan 30 from Orlando Intl. to Bradley Intl., returning Sun, Feb 2, priced at $119 found 4 days ago
Breeze Airways
Sat, Jan 25 - Sun, Jan 26
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$134 Roundtrip, found 11 hours ago
$134
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sat, Jan 25 from Southwest Florida Intl. to Bradley Intl., returning Sun, Jan 26, priced at $134 found 11 hours ago
JetBlue Airways
Fri, Feb 14 - Sun, Feb 23
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Feb 14 from Southwest Florida Intl. to Bradley Intl., returning Sun, Feb 23, priced at $142 found 2 days ago
Spirit Airlines
Wed, May 7 - Sun, May 18
MCO
Orlando Intl.
BDL
Bradley Intl.
$165 Roundtrip, found 1 hour ago
$165
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, May 7 from Orlando Intl. to Bradley Intl., returning Sun, May 18, priced at $165 found 1 hour ago
Spirit Airlines
Mon, Jan 27 - Fri, Jan 31
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$186 Roundtrip, found 2 hours ago
$186
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Mon, Jan 27 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Jan 31, priced at $186 found 2 hours ago
United
Tue, Feb 4 - Sun, Feb 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$198 Roundtrip, found 4 days ago
$198
Roundtrip
found 4 days ago
Select United flight, departing Tue, Feb 4 from Orlando Intl. to Bradley Intl., returning Sun, Feb 9, priced at $198 found 4 days ago
American Airlines
Tue, Feb 4 - Sun, Feb 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$203 Roundtrip, found 4 days ago
$203
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Feb 4 from Orlando Intl. to Bradley Intl., returning Sun, Feb 9, priced at $203 found 4 days ago
Frontier Airlines
Mon, Mar 3 - Sat, Mar 8
DSM
Des Moines Intl.
BDL
Bradley Intl.
$220 Roundtrip, found 17 hours ago
$220
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Mon, Mar 3 from Des Moines Intl. to Bradley Intl., returning Sat, Mar 8, priced at $220 found 17 hours ago
United
Thu, Feb 27 - Wed, Mar 5
CID
Eastern Iowa
BDL
Bradley Intl.
$229 Roundtrip, found 17 hours ago
$229
Roundtrip
found 17 hours ago
Select United flight, departing Thu, Feb 27 from Eastern Iowa to Bradley Intl., returning Wed, Mar 5, priced at $229 found 17 hours ago
Delta
Tue, Feb 25 - Tue, Mar 4
CID
Eastern Iowa
BDL
Bradley Intl.
$237 Roundtrip, found 17 hours ago
$237
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Feb 25 from Eastern Iowa to Bradley Intl., returning Tue, Mar 4, priced at $237 found 17 hours ago
JetBlue Airways
Thu, Jan 30 - Wed, Feb 5
SFO
San Francisco Intl.
BDL
Bradley Intl.
$405 Roundtrip, found 1 day ago
$405
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Jan 30 from San Francisco Intl. to Bradley Intl., returning Wed, Feb 5, priced at $405 found 1 day ago
Alaska Airlines
Wed, Sep 24 - Sat, Oct 4
SFO
San Francisco Intl.
BDL
Bradley Intl.
$517 Roundtrip, found 22 hours ago
$517
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Wed, Sep 24 from San Francisco Intl. to Bradley Intl., returning Sat, Oct 4, priced at $517 found 22 hours ago
Delta
Thu, Jan 30 - Thu, Feb 6
BHM
Birmingham Intl.
BDL
Bradley Intl.
$537 Roundtrip, found 1 hour ago
$537
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Jan 30 from Birmingham Intl. to Bradley Intl., returning Thu, Feb 6, priced at $537 found 1 hour ago

Cheap Flights to Chester

Fall in love at first flight with your vacation to Chester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CEF airport.

What is the cheapest month to fly to Chester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chester are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chester.

What airport is best to fly into Chester?

When you’re planning your trip to Chester, convenience is the name of the game. Luckily, Chester Barnes Municipal Airport is nearby so you can deplane and get going on checking off everything on your Chester must-do list.

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $88, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chester?

The trick to saving a stack of cash on your flight to Chester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $88 right now, why wait?

Chester Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$88

Last Minute Hotel Deals in Chester

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
The price is $143 per night from Jan 26 to Jan 27
$143
includes taxes & fees
Jan 26 - Jan 27
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,345 reviews)
Great stay at the D!
"Had a great time and had great service. We really enjoyed the food and the service at the Delaney House as well!"

Reviewed on Jan 20, 2025

D. Hotel Suites & Spa
Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 out of 5
1254 Riverdale Street, West Springfield, MA
The price is $104 per night from Jan 30 to Jan 31
$104
includes taxes & fees
Jan 30 - Jan 31
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,003 reviews)
"Thank you so much !!"

Reviewed on Jan 20, 2025

Red Roof Inn PLUS+ West Springfield
Tru by Hilton Chicopee Springfield
Tru by Hilton Chicopee Springfield
2.5 out of 5
440 Memorial Dr, Chicopee, MA
The price is $115 per night from Jan 30 to Jan 31
$115
includes taxes & fees
Jan 30 - Jan 31
Stay at this hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
"Brilliant"

Reviewed on Jan 21, 2025

Tru by Hilton Chicopee Springfield
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $108 per night from Feb 6 to Feb 7
$108
includes taxes & fees
Feb 6 - Feb 7
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (480 reviews)
"This was a very clean and beautifully decorated property. I loved the lobby especially. It's a nice place to hang out and read or work. The room was very nice, but the AC/Heating unit was VERY loud and kept going on and off, which kept me awake. I finally turned it off, which meant I had not heat. ..."

Reviewed on Jan 23, 2025

Life House Berkshires
La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MA
3 out of 5
100 Congress Street, Springfield, MA
The price is $123 per night from Jan 29 to Jan 30
$123
includes taxes & fees
Jan 29 - Jan 30
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8.2/10 Very Good! (1,271 reviews)
Great place
"Perfect place to stay while in Springfield. Clean, comfortable, essy to get to, and close to area attractions. Complimentary hot breakfast buffet, but also has a very convenient drive-thru Dunkin' Donuts in a connecting parking lot! Looking forward to our next stay."

Reviewed on Jan 19, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
The price is $92 per night from Feb 6 to Feb 7
$92
includes taxes & fees
Feb 6 - Feb 7
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,000 reviews)
Definitely would go back and recommend
"Very clean and comfortable l. Very quiet also. Breakfast was great kids loved it."

Reviewed on Dec 25, 2024

Quality Inn West Springfield
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $115 per night from Feb 2 to Feb 3
$115
includes taxes & fees
Feb 2 - Feb 3
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,001 reviews)
"Had a great time at this hotel. The rooms are comfortable. The staff is very friendly. Ended up spending Friday and Saturday night hanging out in the bar in the hotel where Carl and George kept us entertained. We had a lot of unexpected fun (I’m not one to hang out in a bar but felt at home)"

Reviewed on Jan 19, 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 out of 5
190 Meadow Street, South Lee, MA
The price is $147 per night from Jan 27 to Jan 28
$147
includes taxes & fees
Jan 27 - Jan 28
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (588 reviews)
"Plenty of room. Good location to local skiing. Clean."

Reviewed on Jan 21, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
See all 792 properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.